The Italian has been one of the best coaches in the world since his foray into management.
Carlo Ancelotti has managed to win the respect of his peers and players alike over a distinguished playing and management career filled with trophies and silent suave. He started his playing career at Parma before switching to Roma and finally to Milan, winning back-to-back Champions League titles and a league title apiece at Milan and Roma.
He has gone on to achieve more in his managerial career, winning three Champions League titles (two with AC Milan, one with Real Madrid) along with league and cup titles across four of Europe’s top five leagues.
So, we take a look at the players who Carlo Ancelotti trusted the most to execute his tactics on the field.
10. Alessandro Nesta – 235 matches
Alessandro Nesta was a rock in defence for the Rossoneri during his time at the club. He arrived in the summer of 2002 from Lazio for €31m and was a constant presence in the legendary backline consisting of fellow greats like Cafu, Maldini, Costacurta and Jaap Stam who went on to rule Italian football during the manager’s tenure.
In a decade long stay, Nesta won two league titles featuring in 326 games in the famous Red and Black kit. 235 of them came under Ancelotti which underlined his importance to the side.
9. Kakhaber Kaladze – 244 matches
You would be forgiven for not knowing about Kakhaber Kaladze given the riches that AC Milan possessed in their defence under Carlo Ancelotti, but the former did have a significant role during the Italian’s time.
The Georgian native moved to Milan in 2001 from Dynamo Kyiv for €16m and featured predominantly as a centre-back, as a backup left-back for Paolo Maldini or occasionally as a defensive midfielder on the left.
He won the Champions League in 2002-03 featuring in every game in the tournament under Carlo Ancelotti and stayed with the Rossoneri till the turn of the decade, playing 284 times out of which 244 came under the legendary manager. It underlined his versatility in the midfield and the backline despite heavy competition.
8. Massimo Ambrosini – 247 matches
Ambrosini spent 18 seasons at Milan after moving from Cesena in 1995 and despite struggling to establish himself as a regular, he did prove to be a useful player when called upon, chipping in with a goal or assist when required to get the job done.
In Milan, he won four league titles and two Champions Leagues and in 344 matches in total, he played 247 of those under the stewardship of Carlo Ancelotti, proving to be a useful addition to the ranks of already established midfielders like Gattuso, Pirlo and Rui Costa.
7. Paolo Maldini – 252 matches
The true embodiment of AC Milan’s history, or perhaps the finest exponent of it. A second-generation AC Milan player succeeding his father Cesare, Paolo spent his entire career with the Rossoneri and won seven Serie A and five Champions League titles in a glorious 25-year stint where he represented Milan a whopping 902 times!
He played a quarter of those games under Carlo Ancelotti (252), leading Milan to a league title and two Champions League titles as part of the dream squad under Ancelotti. The duo also partnered as players in the late 90s.
6. Dida – 267 matches
Dida proved to be the able backup to the almost impregnable backline providing distinguished service to the red half of Milan in a decade-long stay. He represented Milan in 305 matches, Dida was the first-choice custodian for Ancelotti for 267 of those appearances.
He was a pivotal part of the Milan defence in 2002-03 that had the second-best defensive performance in the league that season (30) behind Juventus (29) and won the Champions League as well.
5. Kaka – 270 matches
Kaka’s talent and poise ensconced him as the poster boy of the Milan setup under Ancelotti. He joined in 2003 for a fee of €8.5m, the move turned out to be a masterstroke for both parties as Kaka felt right at home and led the Rossoneri charge on Europe, winning the Serie A and also being voted “Player of the Year” for that season.
His attacking output soared under Ancelotti and he was at the heart of the famed Milan attack. His consistency saw him feature 270 times for Ancelotti during his time at the San Siro during which he produced 95 goals and 84 assists with a goal contribution of 0.67/game.
He enjoyed the best years of his career at Milan under Ancelotti despite moving to Real Madrid for a then-record fee of €68m in 2009.
4. Gennaro Gattuso – 323 matches
If Kaka symbolized the attacking brilliance of AC Milan, Gattuso embodied the Italian fighting spirit. Gattuso was as battle-hardened as they come.
Never the one to shirk away from a challenge or a fist-fight, he was an equally able player with the ball at his feet and a great marshal on the pitch which endeared him to Ancelotti and led to him manning the centre of midfield under Carlo.
Gattuso featured in 323 games under Ancelotti, forming a legendary partnership in the midfield along with Clarence Seedorf and Andrea Pirlo.
3. Clarence Seedorf – 325 matches
Clarence Seedorf along with Gattuso, he formed the heart of Ancelotti’s setup in Milan by becoming an indispensable part of the midfield after slotting in from cross-town rivals Inter.
In 2002-03, Seedorf became the first and only player to have won the Champions League with three different clubs winning previously with parent club Ajax (95-96) and Real Madrid (98-99).
Seedorf, along with Pirlo, became the driving force in the midfield for Milan. He was also an able backup when numbers were needed in defence. He represented Milan 431 times out of which 325 came under Ancelotti where he notched up 49 goals and 55 assists as well.
2. Andrea Pirlo – 327 matches
Dubbed ‘Il Professore (The Professor)’, Andrea Pirlo’s suave and veracity have turned him into one of the most iconic and consummate midfielders of this century, having represented some of the best clubs in Italy and having his fair share of success at that.
Pirlo was a class apart on the ball with his trademark composure and ingenuity. But he possessed razor-sharp awareness of players and spaces in which he could thread the final pass through. He represented Milan 327 times under Ancelotti and probably turned out to be one of the finest exponents in midfield under the watchful eyes of the former Parma manager.
1. Filippo Inzaghi – 331 matches
Ancelotti’s attacking tactics was the perfect foil for Filippo Inzaghi and the Italian turned out to be one of the world’s finest strikers during his time at San Siro.
Inzaghi had a wonderful sense of accuracy and desire to find the back of the net. In 331 games in total at Parma and then at Milan, Inzaghi scored 161 goals under Ancelotti and also laid up 36 assists, becoming the prima facie target man for Ancelotti.